Skip to content
  • There are no suggestions because the search field is empty.
Bailward-20250523-Wim Kerkhoff Headshots-6346

My Story

My name is Wim Kerkhoff.

For nearly two decades, I’ve owned two MSPs: ImprovingIT and Crafty Penguins.

For the last several years, I’ve been completely hands-off. Both companies run under their own presidents while I focus on TopLeft. But it wasn't always this way.

I didn’t hire my first coach until four years into the business. I thought if I just worked harder, the "systems" would eventually click. Instead, I was the bottleneck for everything: tech work, hiring, vendor payments, and sales. I couldn't even take a vacation without checking my Blackberry every ten minutes.

I got to a point that I realized I didn't have a true business until I had an effective manager to support me, real sales & marketing in place, and wasn't the air traffic controller on every task.

What changed? I stopped trying to be the hero. Over the last 15 years, I’ve worked with:

  • Productivity Coaches to stop confusing "busy" with "effective."
  • Traction EOS Implementers to document how decisions actually flow.
  • Marketing & Sales Coaches to move out of reactive mode.
  • A Psychologist (who I still see weekly) to remove limiting beliefs and habits.

Today, my teams own their work. Managers make decisions instead of escalating them. I realized many leaders are stuck with variants of where I was stuck in the past: not having the right mindset, values, people, coaching skills, structures and so forth.

 

What I Actually Do

I don't do regular coaching myself - just don't have the time.

I chat with people like you (MSP owners, service managers, project managers, and team leads) about where they're stuck. Then I'll connect you with the right coach, consultant, or program based on your situation.

Sometimes that's one of the external coaches I've worked with or know well.

Sometimes it's one of TopLeft's programs, like our Accelerator Group Coaching, Agile ScrumMaster Training, or a Rapid Implementation project.

Sometimes it's a combination.

This isn't a revenue thing for me. I don't get paid referral fees. I do this because I wasted four years trying to figure it out alone, and I know what the right coaching can do.

wim

Meet Some of My Coaches

Over the years, I've worked with coaches who specialize in different things. Here are three I've featured on my podcast:

francesco-removebg-preview

Francesco - Mindset & Leadership

Francesco helped me work through the mental blocks that keep leaders stuck. These include control habits, limiting beliefs, and the fear of letting go. We did a podcast together where we talked about the invisible barriers that stop owners and leaders from stepping back.

nate_o_hara-removebg-preview

Nate - Operations & Scaling

Nate focuses on helping leaders build systems and teams that can scale. He's worked with me on delegation frameworks, decision rights, and getting middle managers to actually manage instead of escalate.

Melvyn Bulkes

Melvyn - Agile & Lean Methods

Melvyn is an Enterprise Agile Coach. He helps leaders build teams that improve flow, reduce waste, and collaborate instead of work in silos. His background in large service organizations (IBM, Accenture) gave him deep expertise in workflow, prioritization, and accountability.

I know other coaches who specialize in EOS, sales, marketing, and more. I'll brainstorm some suggestions after our first call.

Who This is For

This makes sense if:

  • You're stuck approving things your team should own
  • Your direct reports escalate instead of deciding
  • You can't take time off without everything falling apart
  • You've got a talented but toxic person you keep making excuses for
  • Your team's priorities get distorted by whoever yells loudest
  • You're waiting for a "superstar hire" that never shows up
  • You're tired of being the bottleneck
  • You're a service manager drowning in ticket escalations your L2s should handle
  • You're a project manager who can't get engineers to own their tasks
  • You're an owner who wants to step back but doesn't trust the team yet

This doesn't make sense if:

  • You think a new tool will fix prioritization or accountability
  • You're not willing to have hard conversations (about toxic people, broken processes, or your own control habits)
  • You want a quick fix that lets you keep running things the same way
  • You're under $500K revenue and still figuring out basic service delivery (you probably need different help first)

 

Types of Coaches In Our Network

This Might Not Be For You

This is not another software tool you can install and ignore.

It won’t work if you:

  • are looking for a quick fix that lets you keep running the business the same way

  • want a tool to solve problems without changing how decisions are made

  • are unwilling to have hard conversations about toxic team members, broken client agreements, or your own control habits

 

This is for you if you are

  • Tired of being the bottleneck that everything depends on

  • Willing to question how decisions are made and who actually owns the work

  • Ready to address the taboo issues you’ve been avoiding, like toxic high performers, unprofitable client agreements, and decision bottlenecks at the top

  • Clear that real change takes effort, repetition, and time

If you just want a tool to surface problems, this isn’t it. TopLeft’s tools make issues visible, and this coaching helps you resolve them.

 

Coach 1

EOS Implementers

  • For MSPs who need clear accountability charts, defined decision rights, and a framework for running their business with less chaos.
Coach 2

Marketing & Sales Coaches

  • For MSPs who need to stop reacting to inbound chaos and build predictable new business.
Coach 3

Productivity & Time Management Coaches

  • For leaders who are busy but not productive, struggling with prioritization and focus.

What Happens Next

Step 1: Book a virtual coffee with me

We'll candidly talk about where you're stuck, what you've already tried, and what success actually looks like for you. 

Step 2: I'll recommend the right path

That might be:

  • Some tactical fixes you can do, from what I've learned in the past
  • A warm intro to a suitable coach
  • One of our own TopLeft coaching programs
  • Or a combination of both
virtual coffee with wim
Capture-3

What About TopLeft?

You don't need TopLeft to benefit from coaching.

But if you do use TopLeft (or decide to), here's how it fits:

TopLeft makes work visible. You see where projects are stuck, which tickets are blocked, who's overloaded. That visibility surfaces the real issues prioritization, ownership, decisions bottlenecking at the top.

Coaching helps you resolve what visibility reveals.

Our Accelerator Group Coaching, ScrumMaster Training, and Rapid Implementation programs combine TopLeft's workflow tools with the habits and culture changes that make them work.

But the coaching stands on its own. If you use a different PSA or workflow tool, we'll help you with whatever you have.

 

The Real Reason I Do This

I spent four years thinking I could figure it out alone.

I was wrong.

The coaches I worked with didn't just help me step back from my MSPs; they helped me build companies that could run without me. That let me eventually focus on TopLeft.

Most MSP leaders are spending their best years stuck in the weeds because they think coaching is for people who are failing.

It's not. It's for people who want to stop wasting time on things their team should own.

Whether you're an owner trying to step back, a service manager buried in escalations, or a project manager who can't get engineers to take ownership; if you're the bottleneck, let's talk!

wim-1

Book a Virtual Coffee with Wim

You’ll speak directly with Wim to check fit and goals. If you decide coaching is right for you, we tailor the engagement through focused coaching or workshops that strengthen your MSP's leadership, speed up project delivery, and create lasting change.